Potassium Carbonate → HCID 178455334, 화합물

HRID 389460노트

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HRID 389460 반응식
[Cl:1][C:2]1[O:12][C:5]2=[C:6]([NH2:11])[N:7]=[CH:8][C:9](I)=[C:4]2[CH:3]=1.[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30](B(O)O)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30]([C:9]3[CH:8]=[N:7][C:6]([NH2:11])=[C:5]4[O:12][C:2]([Cl:1])=[CH:3][C:4]=34)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

참가 물질

6

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HCID 11430Potassium CarbonateHCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amineHCID 178455325HCID 178455325, 화합물

생성물 1

HCID 178455334HCID 178455334, 화합물수율 63.9%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (2 g, 7 mmol), [1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]boronic acid (2.75 g, 8.49 mmol), (1,1′bis-(diphenylphosphino)-ferrocene)palladium dichloride (248 mg, 0.340 mmol) and potassium carbonate (2.35 g, 17.0 mmol) in 1,4-dioxane (20 mL) and water (9.5 mL) was heated to 70° C. for 22 h. The mixture was partitioned between ethyl acetate and water and the aqueous phase extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (10% to 50% ethyl acetate:heptane) followed by trituration with ether:heptane afforded 2.0 g (60%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (s, 1 H), 7.76-7.69 (m, 1 H), 7.62 (s, 1 H), 6.73 (s, 1 H), 4.73 (s, 2 H), 4.17 (tt, J=3.9, 11.6 Hz, 1 H), 3.73 (tt, J=4.3, 10.5 Hz, 1 H), 2.23 (d, J=12.1 Hz, 2 H), 2.09-1.99 (m, 2 H), 1.91 (dq, J=3.5, 11.9 Hz, 2 H), 1.61-1.48 (m, 2 H), 0.92 (s, 9 H), 0.10 (s, 6 H); MS (ESI): 447.39, 449.35 [M+H]+.

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase extracted with DCM
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by ISCO chromatography (10% to 50% ethyl acetate:heptane)

출처 및 근거

ORD 기록
ord-449c54b53f4e430eaca457be091cda8c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

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